General
Preferred name
LANSOPRAZOLE
Synonyms
Lansoprazole (sodium) ()
AG-1749 sodium ()
AG-1749 ()
A-65006 ()
R-(+)-Lansoprazole ()
Prevacid / Ogast ()
A-65006, AG-1749 ()
Lanzor ()
Prevacid 24 hr ()
Ogast ()
Prevonco ()
Prevacid iv ()
Opiren ()
Prevacid ()
NSC-758638 ()
Prevacid Delayed Release ()
Lanzoprazole ()
Takepron ()
Limpidex ()
Prevacid Solutab ()
Lansox ()
Ogastoro ()
Zoton ()
Agopton ()
Lansoprazole-d4 ()
P&D ID
PD000804
CAS
103577-45-3
934294-22-1
Tags
natural product
drug
available
Approved by
FDA
First approval
1995
Drug Status
investigational
approved
Max Phase
Phase 4
Drug indication
Anti-Ulcerative
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE A reported 14-23% of a lansoprazole is eliminated in the urine with this percentage range including both conjugated and unconjugated hydroxylated metabolites. [A177080]
PHARMACODYNAMICS Lansoprazole decreases gastric acid secretion by targeting H+,K+-ATPase, which is the enzyme that catalyzes the final step in the acid secretion pathway in parietal cells. [A177080] Conveniently, lansoprazole administered any time of day is able to inhibit both daytime and nocturnal acid secretion.[A177080] The result is that lansoprazole is effective at healing duodenal ulcers, reduces ulcer-related pain, and offers relief from symptoms of heartburn [A177080] Lansoprazole also reduces pepsin secretion, making it a useful treatment option for hypersecretory conditions such as Zollinger-Ellison syndrome. [A177089][A177080][F4352]
MOA As a PPI, lansoprazole is a prodrug and requires protonation via an acidic environment to become activated. [A174244] Once protonated, lansoprazole is able to react with cysteine residues, specifically Cys813 and Cys321, on parietal H+,K+-ATPase resulting in stable disulfides. [A174244][A177077] PPI's in general are able to provide prolonged inhibition of acid secretion due to their ability to bind covalently to their targets. [A174244]
INDICATION Lansoprazole is used to reduce gastric acid secretion and is approved for short term treatment of active gastric ulcers, active duodenal ulcers, erosive reflux oesophagitis, symptomatic gastroesophageal reflux disease, and non-steroidal anti-inflammatory drug (NSAID) induced gastric and duodenal ulcers. [A4892][A177065][FDA Label] It may be used in the maintenance and healing of several gastric conditions including duodenal ulcers, NSAID related gastric ulcers, and erosive esophagitis.[FDA Label] Lansoprazole prevents recurrence of gastric ulcers in patients who have a documented history of gastric ulcers who also use NSAIDs chronically. [FDA Label] Predictably, it is also useful in the management of hypersecretory conditions including Zollinger-Ellison syndrome. [FDA Label] Lansoprazole is effective at eradicating H. pylori when used in conjunction with amoxicillin and clarithromycin (triple therapy) or with amoxicillin alone (dual therapy). [FDA Label]
METABOLISM Lansoprazole is predominantly metabolized in the liver by CYP3A4 and CYP2C19. [A174244] The resulting major metabolites are 5-hydroxy lansoprazole and the sulfone derivative of lansoprazole. [A174244][FDA Label]
ABSORPTION The oral bioavailability of lansoprazole is reported to be 80-90%[A177053] and the peak plasma concentration(Cmax) is achieved about 1.7 hours after oral dosing.[FDA Label] Food reduces the absorption of lansoprazole (both Cmax and AUC are reduced by 50-70%); therefore, patients should be instructed to take lansoprazole before meals.[FDA Label]
HALF-LIFE One source reports the half life of lansoprazole to be 0.9 - 1.6 hours[A177053], while another source cites 0.9 - 2.1 hours[A174244]. The general consensus is that lansoprazole has a short half life and is approximately 2 hours or less. [FDA Label] These numbers may be misleading since it suggests that lansoprazole has a short duration of action when in practice, lansoprazole can effectively inhibit acid secretion for ~24 hours due to it's mechanism of action. [FDA Label]
DESCRIPTION Lansoprazole is a proton pump inhibitor drug. The approved drug is a racemic mixture of chemical enantiomers; (S)-lansoprazole and . We show the non-stereoisomeric molecule to represent this mixture. (GtoPdb)
TOXICITY The most commonly reported adverse events occurring more frequently in lansoprazole treated patients compared to placebo include abdominal pain, constipation, diarrhea, and nausea.[FDA Label] There is a case report of toxic epidermal necrolysis (TEN), which is a rare but very serious cutaneous reaction, caused by lansoprazole.[A177190] The previously healthy patient presented with symptoms of TEN 15 days after starting lansoprazole to manage peptic disease.[A177190] Although the use of PPI's is rarely associated with TEN, causation should be considered if a patient presents with TEN shortly after newly commencing a PPI.[A177190] ; ; In a single case report, a patient ingested 600 mg of lansoprazole and did not experience any adverse effects or symptoms of overdose.[FDA Label] Overall, lansoprazole is well tolerated with relatively few adverse effects. ; ; Lansoprazole is classified as Pregnancy Category B.[FDA Label] Although there are animal studies that suggest lansoprazole does not cause harm to the fetus, there is still a paucity of human data. Hence, lansoprazole should only be administered to pregnant women if other options with more safety data have been exhausted.; ; It is unknown if lansoprazole is excreted in human breast milk.[FDA Label] It is worth mentioning that lansoprazole has been used safely in infants, and is therefore likely safe to use during breastfeeding.[L6340]
DESCRIPTION Gastric proton pump inhibitor (LOPAC library)
DESCRIPTION H+,K+-ATPase inhibitor (Tocriscreen Total)
Cell lines
2
Organisms
5
Compound Sets
30
AdooQ Bioactive Compound Library
A10513
Axon Medchem Screening Library
3244
Cayman Chemical Bioactives
13627
25227
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL480
ChEMBL Drugs
CHEMBL480
DrugBank
DB00448
DrugBank Approved Drugs
DB00448
DrugCentral
1547
DrugCentral Approved Drugs
1547
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS101713
Guide to Pharmacology
7208
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL480
Mcule NIBR MoA Box Subset
MCULE-8446262134
MedChem Express Bioactive Compound Library
HY-13662
Natural product-based probes and drugs
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Other bioactive compounds
Pandemic Response Box
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Lansoprazole
TargetMol Bioactive Compound Library
T0674
The Spectrum Collection
Tocriscreen Total
External IDs
57
Properties
(calculated by RDKit )
Molecular Weight
369.08
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
3
Aromatic Ring Count
3
cLogP
3.52
TPSA
67.87
Fraction CSP3
0.25
Chiral centers
1.0
Largest ring
6.0
QED
0.75
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
Potassium-transporting ATPase
Proton Pump
PPI
Bacterial
Phospholipase
ATPase,Proton Pump
Selectivity
H+ pump
Pathway
Membrane Transporter/Ion Channel
Anti-infection
Metabolic Enzyme/Protease
MOA
potassium transporting ATPase inhibitor
H+/K+-ATPase Inhibitors
Member status
member
Therapeutic Indication
Antiulcer
Source data